Mainly because the prospect of getting a regular office job like the rest of my friends made me want to gouge my eyes out with a broken Coke bottle.

Anyway, because I hadn’t yet woken up from the compliant, self-hypnotic stupor of higher education, I actually went to the library one day to, ahem, write my business plan.

Ugh. It was awful. I’m pretty sure I died a little bit inside with each page I wrote.

But, I still wrote it. Probably for the same reason most businesspeople obsess over plans:

Because planning preserves the illusion of control.

Or, in my case, because planning helped underwrite the illusion that I knew what I was doing.

Which I didn’t.

I just wanted to feel like a grown up. A professional. A real entrepreneur.

Interestingly, I never once looked at that business plan. Ever again.

And eight years later, my company is thriving in ways I never could have imagined.

LESSON LEARNED: You don’t need a plan to win.

Especially early on in the game.

As I learned in Rework, “When you do write a plan, usually it’s before you’ve even begun. And that’s the worst time to make a big decision.”

Now, it’s not that I’m against planning completely. Rather, I’m against the assumption that planning is always necessary for success.

You’ve probably heard the old saying, “Failing to plan is planning to fail,” right?

Well, let me suggest this:

Failing to plan is planning to prevail.

Let’s explore six strategies to win without planning:

1. Strengthen your why. Planning is a form of how, and how is not your responsibility. Why is what counts. Why is what matters. Why is what makes money.

Decide details later and start focusing on the true motivation behind your current endeavors. Ask questions like: What core values motivated my decision? What do I want this idea to become? With what attitudes do I need to approach this endeavor for me to look back ten years later and still be okay with my decision?

Remember: When you enlist a strong enough why, your plan – your how – will write itself. Otherwise, no amount of planning in the world can compensate for misguided motivations. When was the last time you took inventory of your why?

2. Plans are the preventers of progress. The danger of planning is that it’s a big decision. And big decisions often cause you to prematurely commit to an endeavor that (might) later prove to be unprofitable. Which makes the cognitive dissonance of exiting extremely painful.

That’s another keeper I learned from Rework: “Plans let the past drive the future. They put blinders on you. ‘This is where we’re going because, well, that’s where we said we were going,’ you say. And that’s the problem: Plans are inconsistent with improvisation.”

Be careful. Don’t let the lust for what is familiar block the beauty of what is possible. Are you a victim of your own past commitments?

3. Planning isn’t controlling. In reality, it’s the exact opposite. Especially when you blindly follow a plan that has no relationship with reality. In that instance, it’s no longer a plan – it’s a straightjacket. And unless your name is Houdini, that’s not good for business.

Your challenge will be surrendering control. Focusing more on listening and responding – and less on planning and managing. How vulnerable are you willing to make yourself?

4. Less talkie, more walkie. When I started my publishing and consulting business in 2002, my friend Kate offered me the best piece of advice an author could get: “Stop planning and just write!”

Wow. I didn’t know it was that simple. But she was right. I started to (slowly) learn that great authors don’t “plan” what they’re going to write – they simply show up at the page every morning and listen for what wants to be written.

That’s all creativity is anyway: Active listening.

What’s more, I learned the more you plan; the harder it becomes to invite healthy derailments along the way. And that’s how you miss unlabeled opportunities to grow: When you’re too busy managing the stress of planning to experience the benefits of executing. Don’t close yourself off by making Gods out of your plans. Learn to trust whatever surfaces. What is planning getting in the way of?

5. Practice non-planning when the stakes are low. Try traveling without plans. I recently spent five days in Tokyo with no plans, no agendas, no contacts and no obligation. Didn’t know the language. Didn’t know the culture. I just showed up and let the Japanese winds carry me as they saw fit.

Sure enough, it turned out to be an unforgettable week of getting lost, exploring a perpendicular culture and listening for serendipity to present itself.

Lesson learned: Fewer plans = Greater flexibility. Next time you take a vacation, challenge yourself to cut your planning in half. No need to cut it out completely. Just half. Make plans for the first few days – then go planless for the remainder.

Then, compare the two halves of the trip. You’ll be pleasantly surprised. Or you’ll end up stranded on an island in the South Pacific inhabited by cannibals. Where could you practice non-planning?

6. Redefining the approach. Ready, aim, fire! Ready, fire, aim! Fire, fire, fire! Several problems with these all-too-common approaches. First of all, you’re never really ready. Nor do you need to be ready to take action. So stop waiting for permission.

Secondly, aiming has the tendency to override spontaneity and alienate unseen targets. That’s the big problem with having a plan – you might hit it. Which means you probably weren’t stretching enough. You weren’t uncomfortable enough.

Third, firing is a dangerous word. It’s too violent, highly unfocused and overly aggressive. Plus, if all you ever do is fire, you might find yourself up to your ass in blood and shells. And that’s not the kind of execution you want.

Second, you listen. Or watch. Or observe. And you note the trajectory of your idea to see if the flight plan needs tweaking.

Finally, you leverage. You identify movement by asking, “Now that I have this, what else does this make possible?”

Then, you document everything as it happens. And you reflet on your experiences by extracting lessons learned. Finally, you catalogue those lessons and refer back to them when the time comes to try again. What’s your version of the “Read, Aim, Fire!” approach?

ULTIMATELY: Failure doesn’t come from poor planning – but from the timidity to proceed.

Planning is the gateway drug to procrastination. Don’t get hooked.

JUST REMEMBER: When you don’t know where you’re going, nobody can stop you.

No labels, no limits.

LET ME ASK YA THIS…Will you win without planning?

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